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Lindsey Kilbride, VP of Sales, Trunk Club

Lindsey Kilbride, VP of Sales, Trunk Club

Trunk Club redefines the way we shop. By providing each member a personal stylist – Trunk Club offers a customizable, guided experience that helps men (and now women!) look and feel great.

What’s the story behind your company?

Trunk Club was founded in 2009 by Brian Spaly (CEO), John Tucker (VP Member Experience) and Kevin Price (CFO). The trio came together to redefine the way that men shop. Men inherently understand the value of looking good, but the retail industry offers a narrow range of shopping experiences.

Trunk Club combines the convenience of online shopping with the benefits of the in-store experience, creating a unique service that is custom to each member. Trunk Club does all the work for you, matching you with clothing that is both timeless and modern without hassle or stress.

What were you doing before joining the Trunk Club team?

Immediately before joining the Trunk Club team I was a Senior Sales Director for Mary Kay. I studied Industrial & Operations Engineering and Mathematics at Michigan (Go Blue!) and after several internships with General Motors took a role on the consulting staff at Bain & Company in Chicago. While in my third year at Bain I fell into a part-time role with Mary Kay and realized I love sales…especially with regards to recruiting, training and developing others, so joined their executive team full-time (Pink Cadillac and all) before becoming one of the early Trunk Club teammates in 2010.

How do you stay organized?

In my role as VP of Sales for Trunk Club there are many moving parts; in Dallas alone we have a team of over 100 that ultimately I need to be watching out for. I might not be the most organized person on the planet – but I have set the expectation with my team that if I get sidetracked or run late to please be patient as it’s for good reason.

When a teammate needs to interrupt for a few minutes of my time, or if a scheduled check-in runs late as we hit on some really meaningful topics, I try to be as present as possible and finish the task at hand. If this means I’m five minutes late to my next appointment – trust that I’ll give the same dedication and care to that conversation. Sometimes this means I am at work later than expected or spend a few hours in the evening catching up from home, but that is a choice I am happy to make. I am also a fast talker, a fast reader and a fast typer – so what I lack when it comes to keeping to my calendar I make up for in hustling through the day!

What were some of the challenges you faced when launching and how did you handle them?

Luckily Trunk Club has grown very quickly, but with that growth came the challenges of scaling the business while maintaining the exemplary member experience we pride ourselves on. We’ve faced this challenge in various ways.

The first: hiring the right people. Trunk Club is founded on the high-touch, personal relationships each stylist has with their members. By finding the best people to join our team, those relationships are preserved. Another example: optimizing the business to grow. We have fabulous tech and operations teams that are able to quickly identify and build the tools necessary to keep the company running. We often create our own solutions, which allows our systems to be truly customized, and grow with us.

How do you stay motivated?

Our CEO Brian once told me that it’s possible to inspire people, but true motivation comes from within. I would consider myself a self-motivated person that has wanted to be both successful and happy in all aspects life from an early age. That said, I constantly find inspiration to fuel this passion from my Trunk Club teammates. Watching them take care in providing a great service for our clients as well as their own drive towards professional excellence makes me smile every day when I arrive at, and walk out of, our clubhouse.

How do you delegate and build your team?

Growing a team and developing sales leaders happen to be the two most rewarding and FUN aspects of my role at Trunk Club. I love recruiting, at Mary Kay we called this ‘sharing’ and I loved it then as well. To me, offering someone a fulfilling and rewarding career is one of the greatest gifts I can give. I talk about Trunk Club constantly and am clear about the wealth of opportunities within.

The role of a Sales Director at Trunk Club (where I began my career five years ago) is to build a team of stylists, grow their potential through mentorship and hands-on coaching, and help them move to the next level in their career. We also talk constantly about the idea of ‘finding your replacement’. In order for me to continue achieving and moving forward, I have to build leaders behind me. Delegation comes naturally at our company when people are constantly stepping up to the plate to take on more. 

There’s a lot of interesting insights and science behind the habits of entrepreneurs. How do you start your day?

I typically wake up around 630am, grab my phone and do a quick scan of my inbox over a cup of coffee. This way, if an important note came through during the evening, I don’t have to wait until I’m settled at the office to be on top of it. Most mornings I try to get a run in near White Rock Lake (as I’m expecting twin girls this Fall, these days it’s a brisk walk!) and have breakfast with my husband before heading to the office around 9am. He is in the real estate business and an entrepreneur himself, so by starting the day together we make sure to get some quality time in, no matter how hectic the day/evening might get!

How do you unplug, disconnect, and recharge?

Outside of work, I like to spend time with family and friends and also enjoy the Lakewood neighborhood of Dallas, where we moved last year. To disconnect and recharge, I love to go for a run, listen to music and clear my mind. I also love to read and unplug whenever I can with a few chapters in a good book. I was traveling quite a bit this past year so there are very few titles left in the DC, Dallas, or Chicago airport bookstores I haven’t made my way through.

How do you celebrate successes?

I celebrate successes as often as possible! At Trunk Club we set goals, stretch them and share them with our teammates to hold one another accountable. Throughout the course of each month, we also check in several times with our stylists to celebrate the small wins they have already accomplished. Each of our five Trunk Club offices have an ‘all hands’ meeting to kick off every month where we celebrate bigger wins across teams. Who went above and beyond for a fellow teammate? Who had their personal best month ever? Who got some excellent feedback from a happy client? Who on our tech, sales support, member experience or finance team continues to set the bar high? It’s a time to reward both individual and team efforts.

If you had one piece of advice to give fellow entrepreneurs, what would it be?

Surround yourself with the best people possible.

We don’t always have the right answer at Trunk Club and often fail forward to success, but by having a strong and supportive team in place we have weathered the storms together and come out on top. Culture is not something you can simply define in a mission statement, it is created and sustained by the leaders and teammates you surround yourself with daily.

Success is the goal but failure teaches us a lot. What are some of the biggest lessons you’ve learned as an entrepreneur?

Be confident in your abilities, don’t be ashamed to ask for help, and when it comes down to it – trust your gut. I tell my team constantly that with passion and hard work you can close the talent gap quickly in areas you might not feel as strong. I have countless examples of this in every job I’ve had. Asking for help is a sign of ambition, not weakness…it means you want to get better! Also if something (or someone, when it comes to hiring) just doesn’t feel right, it probably isn’t.